It was a Valentine's Day show, so of course Syd Straw began her performance at City Winery Thursday with a pair of songs about death. "Unraveling," written for her father while he was dying of lung cancer, found Straw calling out to heaven as she strummed jangling guitar chords, and "About to Forget" had her contemplating her dog's demise.

While far from romantic, the songs set the tone of deeply felt emotion that ran throughout Straw's "heartwreck" show, which the idiosyncratic singer has been performing for more than a decade.

That tradition provided a welcome occasion for a rare local appearance by the cult heroine, who lives in rural Vermont. Straw received attention in the 1980s for her work with the Golden Palominos, an indie rock super group that occasionally included the likes of Michael Stipe and Matthew Sweet, and her subsequent solo debut record, but since then her records and Chicago concerts have been exceedingly few and far between.

In the past, Straw has filled her heartwreck shows with covers of other musicians' songs, but for the most part she drew on her own work for this concert, playing her 2008 (and most recent) record "Pink Velour" almost in its entirety.

Straw sang winding melodies in a sensual, breathy alto, filling songs with turtledove coos and pealing cries. A self-described "method singer" who's dabbled in acting, she added a theatrical quality to her delivery as she contorted her long, expressive features on her songs, particularly the jaunty art-pop of "Sphinx."

A four-piece band accompanied Straw with shimmering 12-string and electric guitar and gently rumbling rhythms. The music mined a late-60s country-rock vein indebted to Neil Young, whose "Harvest" Straw performed as an encore, joined by opening act Freedy Johnston.

The songs recounted various pains of the heart, from family drama ("Pink Velour") to career blues ("Actress") to love gone bad ("Storm Warning"). Straw leavened the ache with her clever wit, which carried over from her lyrics to her characteristically outlandish stage patter.

"If he's the best man, why am I marrying you," Straw sang at one point, but on the same song she added "I've had the thorn, I want the rose," hanging on to a hope that had survived all the heartwrecks.